A Lewis Acid-Controlled Enantiodivergent Epoxidation of Aldehydes
ACS CATALYSIS(2023)
摘要
Two epoxidation catalysts, one of which consists of two VANOL ligands and an aluminum and the other that consists of two VANOL ligands and a boron, were compared. Both catalysts are highly effective in the catalytic asymmetric epoxidation of a variety of aromatic and aliphatic aldehydes with diazoacetamides, giving high yields and excellent asymmetric inductions. The aluminum catalyst is effective at 0 degrees C and the boron catalyst at -40 degrees C. Although both the aluminum and boron catalysts of (R)-VANOL give very high asymmetric inductions (up to 99% ee), they give opposite enantiomers of the epoxide. The mechanism, rate- and enantioselectivity-determining step, and origin of enantiodivergence are evaluated using density functional theory calculations.
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关键词
asymmetric catalysis,epoxidation,enantiodivergence,DFT calculations
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